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292710

Sigma-Aldrich

Phenyl β-D-glucopyranoside

≥95.0%

Synonym(s):

Phenyl beta-D-glucoside

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About This Item

Empirical Formula (Hill Notation):
C12H16O6
CAS Number:
1464-44-4
Molecular Weight:
256.25
Beilstein:
87517
EC Number:
215-978-6
MDL number:
MFCD00064089
UNSPSC Code:
12352201
PubChem Substance ID:
24857607
NACRES:
NA.22

Assay

≥95.0%

form

powder

optical activity

[α]25/D −70°, c = 1 in H2O

mp

176-178 °C (lit.)

SMILES string

OC[C@H]1O[C@@H](Oc2ccccc2)[C@H](O)[C@@H](O)[C@@H]1O

InChI

1S/C12H16O6/c13-6-8-9(14)10(15)11(16)12(18-8)17-7-4-2-1-3-5-7/h1-5,8-16H,6H2/t8-,9-,10+,11-,12-/m1/s1

InChI key

NEZJDVYDSZTRFS-RMPHRYRLSA-N

Application

Phenyl β-D-glucopyranoside can be used:
  • As a starting material for the synthesis of various derivatives of β-D-glucopyranosides with potential application as anti-HIV agents.
  • As a model for glycosides in the gas phase for their spectroscopic investigation.
  • As an internal standard in GC and GC-MS quantitative analyses.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis of peptidomimetics based on iminosugar and ?-d-glucopyranoside scaffolds and inhibiton of HIV-protease.
Chery F, et al.
Tetrahedron, 60(31), 6597-6608 (2004)
Anke Reinders et al.
Plant, cell & environment, 29(10), 1871-1880 (2006-08-26)
Plant sucrose transporters (SUTs) are members of the glycoside-pentoside-hexuronide (GPH) cation symporter family (TC2.A.2) that is part of the major facilitator superfamily (MFS). All plant SUTs characterized to date function as proton-coupled symporters and catalyze the cellular uptake of sucrose.
Udayanath Aich et al.
Carbohydrate research, 341(1), 19-28 (2005-11-26)
Reported is an attractive and environmentally friendly method for the synthesis of the title compounds in moderate yield using inexpensive 1,2,3,4,6-penta-O-acetyl-beta-D-gluco- and galactopyranoses as sugar donors, five different phenols as acceptors and H-beta zeolite as the catalyst. The yield (23-28%)
Chunyan Bao et al.
Carbohydrate research, 339(7), 1311-1316 (2004-04-29)
A new hydrogel based on a substituted phenyl glucoside with a Schiff base in the aglycon was synthesized, and the self-assembling characteristics was studied. FTIR spectra, UV-vis absorption spectra and X-ray diffraction (XRD) revealed that pi-pi interactions between the Schiff
V T Edwards et al.
Xenobiotica; the fate of foreign compounds in biological systems, 16(9), 801-807 (1986-09-01)
The metabolic fates of 14C-phenol and its model plant conjugates 14C-phenyl glucoside and 14C-phenyl 6-O-malonyl-glucoside have been compared following equimolar oral dosing to rats (1.2 mg phenol/kg). Rapid excretion of radioactivity in the urine (at least 80% within 24 h)
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